Methylboronic Acid → 3-{4-[4-(5-Fluoro-2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-one

HRID 1804164Notes

Reaction equation

HRID 1804164 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][CH2:27][O:26][C:25]3=[O:29])=[CH:20][C:19]=2[S:30]([CH3:33])(=[O:32])=[O:31])=[O:17])[CH2:12][CH2:11]1.[CH3:34]B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[F:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH3:34])=[C:3]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:28][CH2:27][O:26][C:25]4=[O:29])=[CH:20][C:19]=3[S:30]([CH3:33])(=[O:32])=[O:31])=[O:17])[CH2:12][CH2:11]2)[CH:4]=1

Participants

8

Reactant 4

HCID 139377Methylboronic AcidHCID 522689Potassium FluorideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 547550013-{4-[4-(2-Chloro-5-fluoro-4-methylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-one

Product 1

HCID 673807373-{4-[4-(5-Fluoro-2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-oneYield 11.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-{4-[4-(2-chloro-5-fluoro-4-methylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-one (0.5 g) described in Preparation Example 14, methylboronic acid (479 mg), palladium (II) acetate (90 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (328 mg) and potassium fluoride (930 mg) was added tetrahydrofuran (12 mL), and the mixture was refluxed for 18 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (55 mg).

Workup

  1. temperaturethe mixture was refluxed for 18 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-682f07aba92f451a8ed9228707fcb2de
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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